This paper documents lessons learnt by the IT-leadership team as they played their part in a billion-dollar IT-based transformation in a large Australian retail organization, Coles Myer Limited. The story begins when the new CIO arrived in October 2002, and ends five and a half years later when the CIO resigned, in March 2008. During that period, the IT-leadership team transformed a group of very ordinary divisional IT organizations into an extremely high-performance centralized IT organization—at one stage with IT staff numbers exceeding 2,000. The case concludes with a list of seventeen key success factors for the IT transformation at Coles Myer and a comparison of these with the recommendations from Kotter’s (1995) generic process model of organizational transformation. The case provides unique insights into the way a well-resourced high-energy IT team was built and managed as it attempted to support a broader business transformation.